


What the hell happened to you

by hurtcomfort



Category: Supernatural
Genre: Angry Dean Winchester, Angst, Cute Jack Kline, Dean Winchester Has Nightmares, Dean Winchester Has Self-Worth Issues, Dean Winchester Needs a Hug, Dean/Cas is optional you can see them as friend or nah idc, Emotional Hurt/Comfort, Gen, Good Sibling Dean Winchester, Good Sibling Sam Winchester, Hurt Dean Winchester, Hurt/Comfort, Lawyer Sam Winchester, Sam made it back on Monday
Language: English
Status: In-Progress
Published: 2021-02-22
Updated: 2021-03-04
Packaged: 2021-03-19 03:42:08
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 4,516
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29620071
Author URL: https://archiveofourown.org/users/hurtcomfort/pseuds/hurtcomfort
Summary: Sam made it back on Monday, he became a lawyer and everything was great for him. But everything that happens in the show still happened to Dean. And now Dean is arrested and Sam is his lawyer.
Relationships: Castiel & Dean Winchester, Castiel & Dean Winchester & Sam Winchester, Castiel & Jack Kline, Castiel/Dean Winchester, Claire Novak & Dean Winchester, Claire Novak & Sam Winchester, Dean Winchester & Sam Winchester, Jack Kline & Claire Novak, Jack Kline & Dean Winchester, Jack Kline & Sam Winchester, Jody Mills & Claire Novak, Jody Mills & Dean Winchester, Jody Mills & Sam Winchester
Comments: 8
Kudos: 36





	1. Chapter 1

**Author's Note:**

> WARNING: I don’t own any of these characters except the ones I make up
> 
> This takes place during season 13, before Cas comes back (but he will come back in this) and Dean is still so messed up that he got arrested, and Sam is is lawyer.
> 
> We’re just gonna ignore all the plot holes in this 😁

Sam was having a long day and was beyond ready to just go back to his apartment and call it a day, but Jordan said that this was possibly the biggest case of the year and Sam wasn’t ready to pass up that opportunity. So he took some aspirin, straightened his tie, and got ready to go meet his new client.

***

Dean had screwed up. Completely and utterly screwed up. 

It was a simple hunt, just a demon, but he let his guard down and he didn’t notice when one of the witnesses called the cops after he stabbed the thing with his demon knife. He should’ve known better because now he’s sitting in an interrogation room —which isn’t very uncommon for him— with his hands cuffed and Jack all alone in the bunker.

He still hasn’t gotten his phone call which means he doesn’t know what the kid has gotten himself into, he just hopes that he’s alright.

Jack has barely left his side since the day Dean saved him from those angels 3 months ago. Even if at first Dean didn’t get along with him, he can’t help but admit that the little nephlim squirmed his way into Deans closed off heart. He just couldn’t help it, Jack was kind and so innocently pure, not to mention he was nothing like Lucifer, in fact he was the spinning image of....

He shakes that thought from his head. He can’t think about that here. Not when his lawyer is about to come in. Dean obviously didn’t have one so they assigned him one, they said he was the best one that they have. But coming from them that’s not saying much.

Speaking of the mystery lawyer, Dean hears someone approaching. After a second a tall figure walks in the room. And when he turns around, Dean gasps it’s........

“Sammy”

***

Sam turned around about to go greet this supposed maniac until he hears

“Sammy”

He freezes. No one has called him that since....

“Dean?” He asks

He flips the light switch on and looks at the guy sitting at the table

And sure enough, it’s Dean. 

Sam pauses, taking a moment to look at him. He’s got shorter hair, and a little stubble lining his jaw, there’s a bruise underneath his left cheek and a cut of his lip. He’s no longer wearing their dads leather jacket, instead there’s a navy blue one, on top of a flannel and a grey T-shirt. Sam finally looks up to meet his brothers eyes. Those emerald green eyes that used to be so mischievous and cunning now look tired and haunted. Wow. He hasn’t seen or heard from Dean in probably......13 years. It doesn’t feel like that long, it feels like just yesterday Sam hopped out of the Impala and went back to that tiny dorm in Stanford. But what happened to Dean? He looks so much older, like the world weighed him down to the point where he stopped caring.

Then Dean just starts laughing, a rough, tortured sound. Sams confused, why is he laughing?

“I should’ve known” he gaps out between breaths “out of all the lawyers I could have gotten, it had to be my little brother, one that I haven’t talked to in....how long has it been Sammy?”

Sam recovers from shock and stammers “uhm 13 years I think” 

Dean has now stopped laughing and gets a look on his face 

“13 years? Wow I thought it was longer”

Longer? 

“It sure as hell felt like it’s been longer than that” 

What does that mean? 

“Anyway, how’ve you been Sammy?” 

And suddenly, Sam gets angry, what the hell is he doing? Marching in here and messing up Sams life, and pretending like nothing happened, like they’ve been in contact for the last 13 years. Even though they haven’t, and that’s the way Sam wanted it, and he though that’s what Dean wanted too. So Deans right, why did it have to be him?

“Sammy?” Dean asks again

“It’s Sam.” He says

Dean puts his hands up, or at least as far as they will with the cuffs on 

“Right sorry, Sam how have you been” 

Dean seems genuinely curious so Sam forces himself to calm down, now is not the time or the place for getting angry. 

“I’ve been good Dean” he says “what about you?” 

And honestly a big part of Sam is curious

“I’m fine Sammy” he says doing his trademark smirk 

But it doesn’t reach his eyes

“So” Dean says, slapping a hand on the metal table “can I get that phone call now?” 

Sam can tell he’s avoiding talking to him, but Sams fine with that so he just says

“Ya” and goes over to uncuff his brother 

Dean follows him to the next hall where the phone is and pauses for a moment before dialing a number.

***

Dean knows that he can’t call Jack became the kid still hasn’t figured out how to work a phone. So he calls the only other person he can think of: Jody.

She answers after the first couple of rings 

“Hello?” 

He wants to sigh in relief when he hears her voice, but he restrains himself, Sam is still watching.

“Jody, it’s Dean” 

“Dean! Oh my gosh I’ve been so worried! What happened are you okay?” 

He laughs slightly “yes, I’m good, I’ve just gotten myself into a bit of trouble” 

He hears her sigh “of course you have, so what can I do to help”

He smiles, this is why he called her, he knew she would help

“I’m in jail and I need your help” 

“Jail? Really? You’re gonna be the death of me boy” 

He chuckles. Man he really missed her, he’s just been avoiding her because he knows that both her and Claire know about what happened with his Mom and Cas. And he knew they would wanna walk about it, but he want ready for that.

“So can you come?” 

“Ya I can, where are you?”

“California state prison” he thinks for a moment “and pick up Jack on your way there, he should just be in the bunker” 

“Alright, you got it. I’ll be there as soon as a can. Oh and by the way, Claire wanted to see you” he hears her protest that statement and has to fight the smile on his face “so she’ll be coming too” 

“Okay, I’ll see you soon” 

He hangs up the phone and turns to face his brother. This was going to be a long wait.

***

After they get back to Deans room he looks at the man across from him. A man that used to be a boy. Sam had longer hair, about shoulder length, and has somewhat of a beard on his face. He’s in a fancy suit that makes him seem even taller. 

“Are you just gonna stare at me it are you gonna tell me why you’re here?” 

Dean snorts, he always was straight forward.

“Why don’t you take a look at my file” Dean retorts gesturing to the file in Sams hand.

Sam sighs but looks at the file nonetheless. He looks for a moment and then looks back up at Dean

“Murder and credit card fraud” Sam says aloud   
“I guess I shouldn’t be surprised”

Dean shrugs, trying to keep things casual until Jody shows up.

Sam leans over and whispers to Dean 

“Why are you really here Dean? Was it a hunt?”

Dean snorts 

“Yes it was a hunt Sam” 

“What was it? Werewolf? Ghost? Rathe?” 

“Demon” Dean says bluntly 

“Demons? I though Dad kept those away from us for a reason. That’s a big deal Dean, demons are really dangerous”

Dean laughs

“Dangerous? Please, those things are easy” 

Sam physically recoils.

But Dean changes the subject before he can ask too many questions 

“Well Sammy you’re a big hot shot lawyer now and I need some alone time, so how about you leave and come back when my friend gets here, ya?”

Sam stays silent for a moment but eventually nods

“Ya sure”

And then leaves the room. Leaving Dean alone.

***

As Sam walks down the hall, the question from earlier returns to his mind: What happened to him?


	2. Chapter 2

**Summary for the Chapter:**

> Jody, Jack and Claire come

**Notes for the Chapter:**

> Hope you guys enjoy this!

Dean was sitting in the room, waiting. He never really was a patient person. But he could make do for a while, and according to his watch Jody should be here soon. 

Speak of the devil— well not really, but his kid there—Jody comes walking in the room. 

“Dean!” Jody yells, coming forward to wrap him in a hug

“Hey Jody” he says 

She pulls back, hands still on his shoulders

“What happened?” 

He takes a second to look around and make sure the guards have left before leaning and saying 

“Demon hunt gone wrong”

She nods. That’s another thing he loves about Jody, she doesn’t ask any questions.

“Thanks for coming” he tells her 

She hugs him again

“Of course” 

They stay like that for a minute, savoring the moment, until Sam walks in. 

***

Sam had been watching from a far. The person Dean called was no one that Sam knew, but honestly that wasn’t what was weird, in fact Sam was expecting that. No, what was weird was the fact that the woman he called showed up here with a teenage girl and a guy who couldn’t have been older than 25. Sam doesn’t know those people either. 

The security guard comes and taps him on the shoulder 

“Mr. Winchester, you can go in now”

Sam nods and turns the handle to go back to the room with his brother.

When he opens the door, Dean and the lady pull away from their hug.

“Hi” Sam walks up to the woman 

“Hello” the most woman says, shaking his hand firmly 

“What’s your name?” He asks

“Jody Mills, and you?”

“Sam Winchester” 

Her eyes go wide

“Winchester?!” 

She turns to Dean 

“This is the brother?” 

Dean nods his head

“Wow. Okay then, thanks for the heads up” 

Dean smiles at her sheepishly

“Sorry, guess it kinda slipped my mind” 

Sam smirks, amused with their antics.

Dean turns back to Sam

“So, Sammy, when am I gonna get out of here?”

Sam pauses, unsure of what to say, because honestly, he doesn’t know. Even if Sam is a good lawyer, it would take a miracle for Dean to be exonerated. With all of his crimes, Dean’s lucky he’s not in FBI custody. 

“Dean, I’m not gonna lie, it doesn’t look good”

Dean laughs. What’s so funny? Doesn’t he understand how much shit he’s in?

“Of course it doesn’t look good. I mean when are you gonna slip me the keys so I can make a break for it” 

Sam stares at his brother, utterly speechless. Dean stares right back, his eyes asking the same question his mouth just said.

“I’m not gonna do that Dean!” Sam whisper yells “I have a good thing going here and I’ll be damned if I let you ruin it”

Deans face falls. 

“Oh” he says

He closes his eyes for a minute, and Sam hears him take a deep breath, Jody eying him worriedly from the side.

“No, you’re right, of course” Dean says “umm, just send the kids in, will ya?” 

Sam kinda feels guilty. But he pushes the feeling down and nods at his brother. 

He walks out of the room and goes to fetch the others. When he reaches them they both look up immediately.

The boy stands up and rushes forward to Sam

“Where is he?” 

The boy doesn’t seem angry, just.......scared.

“He’s in an interrogation room” 

He looks at the girl, confused 

She sighs

“It’s where they talk to bad guys” she tells him

He squints and turns back to Sam

“Dean is not a bad guy, why is he in there?” 

“Because the cops think he is” The girl answers before Sam can.

“You guys can go see him” he tells them

They start walking there, Sam following behind so they don’t get lost, but suddenly the boy turns around

“Wait, there’s something familiar about you” he says, stepping closer to Sam.

He walks up so he’s nearly face to face with him

“You’re his brother” 

“How do you know that?” Sam asks, getting ready for a fight.

Even after all these years, he likes to believe he hasn’t gone completely soft.

“I can feel it” the boy says, like it answers everything 

“....okaaay” Sam says 

The boy smiles and continues walk-in with the girl.

Well. That was weird. 

Sam pushes it to the back of his mind, right where all the other questions are.

***

Sam opens the door and lets the 2 people in. 

The boy immediately goes to Dean, who’s now been uncuffed and is standing in the corner of the room with Jody.

Dean sees him and smiles, opening his arms out to the boy who was rushing towards him

“Hey kid” he says

The boy burrows his face into Deans shoulder.

That’s definitely weird, Dean has never really been a physical person. Whenever Sam would hug him, Dean would tense up and carefully peel Sams lanky arms of off him and tell Sam he was busy. 

A lot has certainly changed.

The girl walks over to him after the boy finally detaches and gives Dean another hug. And once again, Dean takes it with no complaint, in fact, he seems to lean into it. 

Sam slyly steps a little closer, trying to hear what they’re saying. He hears the girl whisper to Dean

“I’m sorry about Cas” 

Who’s Cas?

Dean lets out a shaky breath

“Me too” 

Well whoever this Cas person is, was clearly important to Dean.

Suddenly Sam feels guilty again. And he gets an idea, maybe he can help his brother. 

“Hey” he says, grabbing their attention “I think I can help get you out of here Dean” 

The boy perks up, and Dean has to put a hand on his shoulder to keep him from jumping 

“I can help you with this Dean, but we have to do it right. Which means I need to be your actual lawyer, and maybe, if we’re lucky, I can get most of your charges cleared” 

Dean asks “how long will it take” 

“With your charges?” Sam laughs “a while”

Dean goes quiet for a minute and then says

“Okay, I’m in” he points to the rest of his group “only if Jack, Claire, and Jody can come though” 

Jack and Claire. Nice to finally get some names.

“Sure, they can come” Sam says, smiling when he sees their faces light up “do you have anywhere to stay?”

Dean shakes his head.

Sam sighs, he has a feeling he’s gonna regret this but “you can stay at my place” 

Dean looks like he’s about to protest but Jody jumps in faster

“That would be wonderful, thank you Sam” 

After that, Sam leaves them to talk about whatever they need, while he goes to find a way to get Dean out.

He has a feeling this is going to be a weird adventure.

**Notes for the Chapter:**

> This one is a little shorter, but I’ll try and make the next one longer!


	3. Chapter 3

**Summary for the Chapter:**

> A few things get sorted out

**Notes for the Chapter:**

> Btw I know nothing of the law, so forgive me for the incorrect things that I say.

Dean sits down in the cushioned chair that’s in the lobby of his little brothers office. It’s not the most comfortable thing in the world but compared to the metal chair he’s been sitting in for last 8 hours, it feels like a new foam mattress.

Jody is sitting at a table with Jack, teaching him poker and Claire is sitting next to Dean. 

“Dean?” 

He looks over to see Claire’s blue eyes staring at him 

“Yeah?” 

She pauses, like she’s choosing her next words carefully. Then she places a hand on his arm

“I miss him too” 

Dean tenses, he’s still not ready to talk about that

She seems to sense what he’s feeling so she adds

“It’s okay, you don’t have to say anything, I just wanted to let you know” 

He forces himself to relax again and puts his hand on hers, covering where it is on his arm

“He really cared for you” he tells her

She gives him a shaky smile, tears building in her eyes

“The feeling was mutual” she says

He nods, swallowing the lump that’s building in his throat.

Claire lays her head on his shoulder and he lays his head atop hers. He smiles a little, closing his eyes.

***

Sam listens from the hallway. Adding to his list of never ending questions. So far he’s got quite a few, like:

Who’s Cas?

Are Claire and Jack Deans children?

Or are they Jodys?

Why does Dean not wear their dads leather jacket anymore?

Why is he hunting demons?

Why did he say demons were an easy hunt?

How did Jack know Sam was Deans brother?

Does Dean talk about him?

And so many more. 

Sam pushes his thoughts down, walking out of the hallway to go get Dean and his friends. 

“Hey” he says, grabbing their attention

Jack and Jody look up from where they were playin cards, and Claire takes her head off of Deans shoulder, looking up at Sam 

“Hey” Dean replies

“So I got you bailed out for now and your trial is going to be in 2 months”

Sam is lucky that he had so many favors to collect, like when he took took an extra shift so that Jordan could go help his wife have a baby, and when he covered for Alyssa when she needed to leave the court room. And things like that. 

“That’s a long time” Jack says walking over to them, Jody trailing after him

Sams about to tell him that they’re lucky that he’s even getting a trial at all but Dean puts up a hand to stop Sam before he even starts, then turns to Jack

“It’s actually not that long, it’ll be okay” 

Jack still looks a little unconvinced but Dean just nods reassuringly and Jack seems to relax at that.

It’s a bit unsettling, seeing Dean being so soft and kind with Jack and Claire. He’s only seen them interact for a few hours but he can already tell, and Sams only ever seen Dean do that with him, when they were kids. 

“So can we go?” Claire asks

“Ya, we can go back to my place now” Sam tells them, gesturing for the door.

They all shuffle out of the room and eventually it’s just Sam, he sighs, 2 months. He somewhat agrees with Jack, it’s going to feel very long.

***

Dean walks out of the building, surprised to see that it’s already dark outside. He’s not sure if he’s happy to get out of there, or angry that he was there in the first place, but either way he’s grateful that Sam is letting them stay with him because Dean really doesn’t have the money to pay for a hotel for 2 months. However, it’s still weird to see Sam, his little brother who’s not so little anymore.

For Dean it feels like a lifetime since he last saw him. Between Lucifer, and Purgatory, and stopping 2 apocalypses, and all the loss and pain of the last 13 years, it just makes it feel so much longer. And technically if he’s counting his time in hell, then for Dean it has been closer to 50 years. 

He shakes his head, getting rid of the thoughts of Hell. Even after 9 years, he hasn’t truly gotten over his time there, but then again he doesn’t really think there’s a crash course on PTSD from soldiers in hell. 

“You okay” he feels Jody’s hand on his arm

“Ya, just thinking” he says

He looks around, he didn’t even realize that he already made it to the Impala.

Jody nods her head and tosses him the keys she must have acquired from the box in the office that was containing his personal items. He catches them with ease and hops into the car, Jack taking his place in the front and Jody and Claire getting in the back. 

He starts the car and takes comfort in the familiar engine of his baby. It hasn’t even been a day and he was already missing the Impala. 

He looks out the window and sees Sam getting into his own car, a Kia. Not the best, but not the worst either. It’s a safe car, so he’ll give him points for that. Sam pulls out of the parking lot and Dean starts tailing him.

Jack looks over to him

“Are you okay?”

Damn this kid has been his weakness since....well not the moment they met, but soon after. 

“I’m good, kid” 

Jack nods and turns his head to look out the window. So much like Cas. 

He breaths in the scent of his car. The only true home he’s ever had until the bunker. 

He has a feeling the next part is going to be chaos.

**Notes for the Chapter:**

> I’ll hopefully work on it more tomorrow, For now, enjoy this!


	4. Chapter 4

**Summary for the Chapter:**

> Everyone arrives at Sams place but when the brothers finally get a moment alone Sam realizes just how much Dean has changed.

**Notes for the Chapter:**

> Sorry for not updating in a bit, but I hope you like it!

Sam had a nice place, it was small but cozy, unlike the bunker that was big but practically empty. But there was a bigger difference between the bunker and this apartment, the bunker felt like home, and this place didn’t. Which is why, despite being exhausted, Dean knows that he’s not going to be able to truly relax here. 

“Dean?” Jack pulls him from his thoughts 

Dean turns to look at him 

“Ya kid?” 

“Sam says that we should go get settled in our rooms” 

Dean nods, ready to tell the kid to go so that he can be alone, but pauses when he sees Jacks unsure expression

“Something wrong?” He asks 

Jack sighs

“It’s just that...........we’ve never spent a night apart” 

It was true, ever since Jack showed up Dean would try and get him to sleep in his own room, but every night Dean would wake up with Jack sleeping on floor next to him. Even though Dean would never admit it to himself, he liked having someone else in there with him. 

He stands up from the bed that was in his brothers guest room and walks over to the boy, placing a hand on his shoulder 

“I know bud, but how about you try and sleep in the room that Sam gave you, and if you can’t then you can come back in here, okay?” 

Dean gives him an encouraging smile, just like he used to do for Sam.

Jack frowns a bit but nods eventually 

“Okay, thanks Dean” 

Dean pats his shoulder 

“Of course” 

Jack leaves and Dean sits back down on the bed, placing his head in his hands, it’s been a long day, well actually a long couple of months, ever since the events that happened during Jacks birth, Deans been tired since he left that retched island, the place where he lost everything but gained someone he didn’t know he needed. But no matter how much Jack helps, he can’t replace the hole the Cas and mom left, no one can. 

“You okay?” 

He jumps, ready for a fight, but relaxes slightly when he sees Sam standing in the doorway, arms full of blankets.

“Ya, I’m fine” 

Sam gives him the classic bitch face and comes over to sit down next to Dean, setting the blankets on the nightstand next to them

“It doesn’t look like it” 

“Well I am” Dean snaps

Sam holds his hands up in mock surrender 

“Okay, okay, just making an observation” 

Dean sighs forcing himself to plaster on a smile

“You always were good at those, Sammy” 

Sam smiles

“Ya, I was, why do think I’m a lawyer now” 

They both laugh

“Fair point” 

It goes silent, both of them sitting there awkwardly, but then Sam moves, shifting until his entire body is facing Deans. 

“Dean, who is Cas?”

And Deans heart shatters in two 

***

Sam regrets asking the question the moment he sees the look in his brothers emerald eyes, he looks like he’s no longer here at all, he’s just staring at Sam with glazed eyes and a somewhat closed off expression. He couldn’t help it though, he desperately wanted to know who this guy was, because Dean clearly cared for him, and Sam wants to know why he isn’t here now, did he leave, or something worse? Lord knows that the Winchesters have a track record of tragedy striking right when they get close to people. 

He’s about to retract the question when he hears his brother mumble 

“How do you know about him?”

His voice sounds so soft and sad that it makes Sams heart ache in sympathy. 

“Well, I uh, heard you talking about him with Claire” 

Dean nods and takes a shaky breath, his eyes filling with tears. That sight makes Sam want to cry himself, he rarely ever saw Dean cry when they were little, even on nights when Sam would hear him gasp awake, mumbling their mother’s name, not even when Dean would come limping into Sams room late at night after a particularly bad fight with Dad, not even when Sam left for Stanford. But then again, just because Sam didn’t see it, doesn’t mean it didn’t happen. 

Dean lifts his head up and meets Sams eyes

“It doesn’t matter” 

Sam scoffs before he can stop himself 

“Really Dean? This is the first time I’ve probably ever seen you cry, and it doesn’t matter?” 

Deans gaze go hard and he brings his hand up to roughly wipe at his eyes, ridding his face of the few treacherous tears that escaped 

“It’s none of your business Sam!” He snaps 

Sam flinches back, he should’ve stopped, but he couldn’t help himself, he wanted to know who the person was that could have such an effect on his brother, the brother that was tough and badass, the brother that was a soldier. 

Deans head drops and Sam hears his broken sigh

“Dean?” He asks carefully

Dean looks up, smiling sadly 

“Cas was my best friend” 

“Was?” 

“Was. He’s.........gone now” 

His brothers voice wavers on the last part and he doesn’t miss the way Dean hesitated when he said gone

“What do you mean gone?” 

“He’s just gone! Okay?” 

Honestly Sam should count himself lucky he got this much out of his older brother

“Okay, ya” 

Dean looks at him guiltily 

“Look Sam, there’s a lot that’s happened in the past 13 years, more than you could possibly imagine” 

Sam places a hand on his brothers arm

“Dean, you can tell me okay? I’m still the same person I was” 

Dean removes Sams hand from his arm

“I’m not” 

Sam stares at his brother for a second before standing up and walking out, sparing one last glance at his brother.

***

Jack gasps awake, sweat covering his body, and looks around, remembering where he is. He takes a few deep breaths, just like Dean taught him, and lays back down on his pillow. A single tear slips down his cheek as he whispers the name of the only person who can soothe him

“Dad” 

***

Cas wakes up in a corn field, with a voice echoing in his head.

**Notes for the Chapter:**

> Guess who’s coming in the next chapter 😏


End file.
